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Diethyl Pyrocarbonate → (Z)-2-[ethyl-(4-fluorophenyl)sulfonyl-amino]-N-[[2-[4-(trifluoromethoxy)phenyl]-4-pyridyl]methyl]but-2-enamide

HRID 1479842
Notes
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Reaction equation

HRID 1479842 reaction equation
[CH2:1]([N:3]([S:10]([C:13]1[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=1)(=[O:12])=[O:11])/[C:4](=[CH:8]\[CH3:9])/[C:5]([OH:7])=O)[CH3:2].CCOC(OC(OCC)=O)=O.[F:31][C:32]([F:49])([F:48])[O:33][C:34]1[CH:39]=[CH:38][C:37]([C:40]2[CH:45]=[C:44]([CH2:46][NH2:47])[CH:43]=[CH:42][N:41]=2)=[CH:36][CH:35]=1>C1COCC1>[CH2:1]([N:3]([S:10]([C:13]1[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=1)(=[O:12])=[O:11])/[C:4](=[CH:8]\[CH3:9])/[C:5]([NH:47][CH2:46][C:44]1[CH:43]=[CH:42][N:41]=[C:40]([C:37]2[CH:36]=[CH:35][C:34]([O:33][C:32]([F:49])([F:31])[F:48])=[CH:39][CH:38]=2)[CH:45]=1)=[O:7])[CH3:2]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 3051Diethyl PyrocarbonateHCID 68759664[2-[4-(Trifluoromethoxy)phenyl]-4-pyridyl]methanamineHCID 90384190(Z)-2-[ethyl-(4-fluorophenyl)sulfonyl-amino]but-2-enoic acid

Product 1

HCID 90384243(Z)-2-[ethyl-(4-fluorophenyl)sulfonyl-amino]-N-[[2-[4-(trifluoromethoxy)phenyl]-4-pyridyl]methyl]but-2-enamideYield 18.1%

Reagents, catalysts & solvents 1

HCID 8028
Tetrahydrofuran
Solvent

Procedure

Acid 11B (574 mg, 2 mmol) was dissolved in 10 ml of THF and at rt DEPC (1.1 equiv, 0.3 ml) and [2-[4-(trifluoromethoxy)phenyl]-4-pyridyl]methanamine 21B (1.1 equiv., 590 mg) were added to the solution. The mixture was stirred at rt overnight then evaporated. The residue was dissolved in AcOEt (30 ml) and washed with water (1×20 ml) and brine. The organic phase was dried over sodium sulfate and concentrated under vacuum. The purification of the crude by chromatographic column (1:1 EtOAc:petroleum ether) afforded 195 mg of a white solid. Yield=18% 1HNMR (DMSO, 200 MHz) δ 1.00 (3H, t, J=7.2 Hz), 1.46 (3H, d J=7.4 Hz), 3.43 (2H, q, J=7 Hz), 4.40 (2H, d, J=6 Hz), 6.83 (1H, q, J=7 Hz), 7.25 (1H, dd, J=6.4 Hz), 7.42 (4H, m), 7.85 (3H, m), 8.18 (2H, d, J=8.2 Hz), 8.60 (1H, d, J=5 Hz), 8.74 (1H, bt) [M+1] 538.1 (C25H23F4N3O4S requires 537.53).

Workup

  1. additionwere added to the solution
  2. customthen evaporated
  3. dissolutionThe residue was dissolved in AcOEt (30 ml)
  4. washwashed with water (1×20 ml) and brine
  5. dry with materialThe organic phase was dried over sodium sulfate
  6. concentrationconcentrated under vacuum
  7. customThe purification of the crude by chromatographic column (1:1 EtOAc:petroleum ether)

Sources & evidence

ORD record
ord-c5886bcf2d86482e8e294c95cd2aba07
Source dataset
uspto-grants-2016_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09409864B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes